Synthesis of an Enkephalin Analogue Containing an α,α-Disubstituted Heterocyclic Aminophosphonic Acid

Abstract

Synthesis of a phosphonopentapeptide enkephalin analogue was achieved from heterocyclic aminophosphonates via the coupling of Boc-Tyr-Gly-Gly-OH with phosphonodipeptide. The latter was formed by coupling Boc-Phe-OH with N-terminal α,α-disubstituted heterocyclic α-aminophosphonates.

GRAPHICAL ABSTRACT

Keywords:

• Aminophosphonate
• enkephalin analogue
• pentapeptide
• phosphonopeptide
• thiopyran

Acknowledgments

The authors thank Mr. Ronny Wahlström and Ms. Alice Six for technical assistance.